Every fundraiser knows that moment.
You’re sitting across from a major prospect. The pitch is going well… but you can’t tell if it’s time yet to make the ask.
I remember one such meeting vividly.
The donor had deep pockets, the potential was huge, and our founder was speaking beautifully. Still, I sensed the timing wasn’t right.
So I jumped in with four simple words:
“How does that sound?”
Those words turned out to be worth six figures — and taught me one of the most powerful lessons in fundraising.
Because of that small check-in, the prospect voiced an uncertainty about our project — something we hadn’t realized was holding him back.
Once he shared it, we could address it. I watched his expression change as we clarified our case.
Just to be sure, I asked again:
“Is there anything else?”
There wasn’t.
That’s when I nodded to the founder to go in with the solicitation — a multi-year, high-level ask.
Then came the longest ten seconds of silence I can remember.
Finally, the prospect spoke.
With a six-figure commitment — the largest I’d ever helped close.
For many of us, talking about our work is easy. We’re passionate about what we do.
It’s the transition to the actual ask that feels tricky.
Partly because asking for money can feel uncomfortable.
And partly because, in fundraising, timing is everything.
Ask too early, and you lose the gift.
Ask too late, and you miss the moment.
So how do you know when the time is right?
My four-word check-in — “How does that sound?” — is the bridge.
It helps you and your prospect quietly gauge:
“Where are we at? How are you feeling about this? Is there anything holding you back before we move forward?”
Often, donors do have hesitations.
Questions. Doubts. Something they’re unsure about — but won’t say unless you give them permission.
And sometimes, they’re not even sure what’s bothering them until you help them find it.
When you surface those objections early, you can address them — and clear the runway for your ask.
Objections aren’t obstacles.
They’re allies.
They show you exactly what needs to be resolved before your prospect can say yes.
Those four words — “How does that sound?” — are my gift to you this week.
Use them well.
Have a fabulous fundraising week,
Avraham
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